Antiplasmodial alkaloids from bulbs of Amaryllis belladonna Steud

Bioorg Med Chem Lett. 2018 Jan 1;28(1):40-42. doi: 10.1016/j.bmcl.2017.11.021. Epub 2017 Nov 11.

Abstract

A bioassay-guided fractionation and chemical investigation of Amaryllis belladonna Steud. bulbs resulted in the isolation and identification of the new crinane alkaloid 1,4-dihydroxy-3-methoxy powellan (1), along with the 3 known crinane alkaloids 2-4 and the two lycorane alkaloids 5-6. The structures were elucidated by interpretation of combined HR-ESIMS, CD and 2D NMR spectroscopic data. Among these isolated compounds the lycorane-type alkaloid acetylcaranine (5) exhibited strong antiplasmodial activity, while compounds 3 and 4 were moderately active, and compounds 1 and 6 were inactive.

Keywords: Amaryllis belladonna; Antiplasmodial; Bioassay-guided; Crinane; Lycorine.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology
  • Amaryllidaceae Alkaloids / chemistry*
  • Amaryllidaceae Alkaloids / isolation & purification
  • Amaryllidaceae Alkaloids / pharmacology
  • Antimalarials / chemistry*
  • Antimalarials / isolation & purification
  • Antimalarials / pharmacology
  • Asparagales / chemistry*
  • Asparagales / metabolism
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Circular Dichroism
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Plant Extracts / chemistry
  • Plant Roots / chemistry
  • Plant Roots / metabolism
  • Plasmodium falciparum / drug effects
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • 1,4-dihydroxy-3-methoxypowellan
  • Alkaloids
  • Amaryllidaceae Alkaloids
  • Antimalarials
  • Plant Extracts